A Thiourea-Based Rotaxane Catalyst: Nucleophilic Fluorination Phase-Transfer Process Unlocked by the Mechanical Bond
Julio Puigcerver1, Juan S Dato-Santiago1, Mateo Alajarin1
1Departamento de Química Orgánica, Facultad de Química, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, E-30100 Murcia, Spain.
None:
We report a five-component clipping approach using activated isophthaloyl-derived esters to synthesize an amide-based thiourea rotaxane. This method overcomes acyl chloride limitations with nucleophilic thiourea threads. The steric hindrance of the mechanical bond enables, for the first time, an interlocked thiourea as a hydrogen-bonding phase-transfer organocatalyst in nucleophilic fluorinations. This highlights how mechanical bonds expand thiourea catalysis to processes previously incompatible with conventional catalysts.
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